Protonation of 1,1,3,3-tetramethyl-2-X-guanidine has been shown to occur on the imino nitrogen when X is electron donating (Ref: Liler, M. Adv. Phys. Org. Chem. 1975, 11, 267.; Adv. Phys. Org. Chem. 1975, 11, 306.) A controversy about which nitrogen is protonated when X is – NO2 was solved by a Hammett plot of the basicity of the guanidine vs. the o constants of the substituents-including nitro. The plot was linear, with a negative p, for all substituents. What do you conclude about the protonation site when X = NO2? What would you expect the plot to look like if an amine nitrogen were protonated when X = NO2? %3D CH3 H3C-N H3C-N CH3

Protonation of 1,1,3,3-tetramethyl-2-X-guanidine has been shown to occur on the imino nitrogen when X is electron donating (Ref: Liler, M. Adv. Phys. Org. Chem. 1975, 11, 267.; Adv. Phys. Org. Chem. 1975, 11, 306.) A controversy about which nitrogen is protonated when X is – NO2 was solved by a Hammett plot of the basicity of the guanidine vs. the o constants of the substituents-including nitro. The plot was linear, with a negative p, for all substituents. What do you conclude about the protonation site when X = NO2? What would you expect the plot to look like if an amine nitrogen were protonated when X = NO2? %3D CH3 H3C-N H3C-N CH3

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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